Amicus Curiae Brief — Ross William Ulbricht, Petitioner v. United States

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No. 17-950

IN THE

Supreme Court of the United States

ROSS WILLIAM ULBRICHT, PETITIONER,

v.

UNITED STATES OF AMERICA, RESPONDENT.

ON PETITION FOR WRIT OF CERTIORARI

TO THE UNITED STATES COURT OF APPEALS

FOR THE SECOND CIRCUIT

____________________________

BRIEF OF NATIONAL LAWYERS GUILD,

AMERICAN CONSERVATIVE UNION FOUNDATION CENTER FOR CRIMINAL JUSTICE

REFORM, FREEDOMWORKS, HUMAN

RIGHTS DEFENSE CENTER, NANCY

GERTNER, NATIONAL COALITION TO

PROTECT CIVIL FREEDOMS, PARTNERSHIP FOR CIVIL JUSTICE FUND, AND PEOPLE’S LAW OFFICE AS AMICI CURIAE IN

SUPPORT OF PETITIONER

Prof. Zachary Wolfe

The George Washington

University

2100 Foxhall Rd, NW

Ames Hall 218

Washington, DC 20007

zwolfe@gwu.edu

(202) 242-5130

Heidi Boghosian

Counsel of Record

A.J. MUSTE MEMORIAL

INSTITUTE, INC.

168 Canal Street, 6th Fl

New York, NY 10013

heidiboghosian@gmail.com

(917) 239-4999

LEGAL PRINTERS LLC, Washington DC ! 202-747-2400 ! legalprinters.com

i

QUESTIONS PRESENTED

1. Whether the warrantless seizure of an individual’s

Internet traffic information without probable

cause violates the Fourth Amendment.

2. Whether the Sixth Amendment permits judges to

find the facts necessary to support an otherwise

unreasonable sentence.

ii

TABLE OF CONTENTS

Questions Presented ................................................... i

Table of Authorities .................................................. iv

Statement of Interest ..................................................1

Summary of Argument ...............................................1

Argument.....................................................................2

I. This Court should resolve the question

of the privacy interest in online activity ........2

A. Online activity has extraordinary

social importance and requires

constitutional protection .............................5

II. To ensure that judges do not unfairly

punish a defendant in violation of

the Sixth Amendment to the U.S.

Constitution, sentences must be

based on facts proven at trial...........................7

A. Jurors’ historic role as a check against

unbridled judicial power has

diminished, to the detriment

of the rule of law .......................................11

B. Sentencing must be limited to facts

admitted by the defendant or supported

by jury findings .........................................14

iii

C. Judicial fact-finding in this context is

particularly troublesome and

certiorari presents an appropriate

vehicle to address this issue .....................16

1. Confusion and fear, related to

misunderstood technology,

and highly prejudicial murdersfor-hire and drug-related fatalities,

impermissibly tainted sentencing .......16

2. Constitutionally irrelevant victim

impact statements factored into

sentencing bias ....................................18

D. Judicial expressions of hostility to

petitioner’s ideology undermines

first amendment values and public

perception of fairness ................................20

E. Fact-finding should be entrusted

to juries, not judges ...................................21

Conclusion .................................................................24

Appendix .................................................................. A-1

iv

TABLE OF AUTHORITIES

Cases

Abrams v. United States,

250 U.S. 616 (1919) ..........................................5

ACLU v. Reno,

521 U.S. 844 (1997) ..........................................5

Apprendi v. New Jersey,

530 U.S. 466 (2000) ..........................................7

Balzac v. Porto Rico,

258 U.S. 298 (1922) ........................................13

Blakely v. Washington,

542 U.S. 296 (2004) ..................................14, 15

Board of Education v. Pico,

457 U.S. 853 (1982) ..........................................5

Booth v. Maryland,

482 U.S. 496 (1987) ........................................18

Carpenter v. United States,

137 S. Ct. 2211 (2017) ......................................3

Duncan v. Louisiana,

391 U.S. 145 (1968) ........................................21

New York Times Co. v. Sullivan,

376 U.S. 254 (1964) ........................................22

Riley v. California,

134 S. Ct. 2473 (2014) ..............................2, 3, 6

Rita v. United States,

551 U.S. 338 (2007) ........................................15

Smith v. Maryland,

442 U.S. 735 (1979) ..........................................4

Stanley v. Georgia,

394 U.S. 557 (1969) ..........................................5

Texas v. Johnson,

491 U.S. 397 (1989) ........................................21

United States v. Davis,

785 F.3d 498 (11th Cir. 2015) ......................4, 7

v

Cases continued

United States v. Jones,

565 U.S. 400 (2012) ..........................................4

United States v. Ulbricht,

858 F.3d 71 (2d Cir. 2017) ......................3, 6, 19

United States v. Booker,

543 U.S. 220 (2005) ........................................11

Zant v. Stephens,

462 U.S. 862 (1983) ........................................18

Statutes

The Federal Sentencing Guidelines

18 U.S. Code § 3553 ....................................8, 13

Communications Decency Act

47 U.S.C. § 230 .................................................5

Constitutional Provisions

U.S. Const. Amend. IV ...................................... passim

U.S. Const. Amend. VI ...................................... passim

Other Authorities

1 J. Bishop,

Criminal Procedure § 87,

(2d ed. 1872) ...................................................15

2 John Adams's Works (1771) ..................................12

12 Angry Men (Orion-Nova 1957) .............................23

Akhil R. Amar,

The Bill of Rights: Creation &

Reconstruction 83 (1998)................................11

Alexis De Tocqueville,

Democracy in America,

(The Century Co. 1898, 1st ed.) .....................22

vi

Other Authorities Continued

Andy Greenberg,

The Silk Road Creator’s Life Sentence

Actually Boosted Dark Web Drug Sales,

(May 23, 2017, 10:00AM) .................................9

Ashley Nellis,

Still Life America’s Increasing

Use of Life and Long Term

Sentences, The Sentencing Project,

May 3, 2017 ......................................................8

Bryan Denson,

Global meth dealer from Vancouver

gets lighter sentence because of U.S.

agents' 'Silk Road' corruption,

The Oregonian/OregonLive

(Nov. 5, 2015, 3:15PM),

http://www.oregonlive.com/pacificnorthwest-news/index.ssf/2015/11/global_silk_road_

meth_dealer_f.html) .........................................9

Bryan Myers and Edith Greene,

The Prejudicial Nature of

Victim Impact Statements:

Implications for Capital

Sentencing Policy, 10 Psych. Pub.

Pol. & L. 492 (2004) ........................................18

Christine Scott-Hayward et al.,

Does Privacy Require Secrecy?

Societal Expectations of Privacy

in the Digital Age,

43 Am. J. Crim. L. 19 (2015) ........................2, 4

Editorial, The Right to Receive Ideas,

Wash. Post, Apr. 12, 1969 ................................5

vii

Other Authorities Continued

Federal Bureau of Prisons,

Find An Inmate,

https://www.bop.gov/inmateloc/,

(last visited Jan. 27, 2018) .............................10

George P. Shultz and Pedro Aspedec,

The Failed War on Drugs,

New York Times, Op Ed,

Dec. 31, 2017 ...................................................21

Harry Kalven, Jr. and Hans Zeisel,

The American Jury, 499 (1966)......................23

Human Rights Watch,

With Liberty to Monitor All:

How Large-Scale US

Surveillance is Harming

Journalism, Law, and

American Democracy, July 28, 2014 ................6

Jason Meisner,

Biggest dealer on underground

Silk Road given 10 years in prison,

Chicago Tribune, May 29, 2015 .......................8

Jed Rubenfeld,

The End of Privacy,

61 Stan. L. Rev. 101 (2008) ..............................6

Law Enforcement Struggles to Police

“Dark Web,” IACPCybercenter.com,

http://www.iacpcybercenter.org/

news/law-enforcement-strugglespolice-dark-web/ (last visited

Jan. 27, 2018) .................................................17

viii

Other Authorities Continued

Lee Matthews,

What Is Tor, And Why You

Should Use It To Protect

Your Privacy, Forbes.com

(Jan. 27, 2017, 2:30PM),

https://www.forbes.com/sites/leemathews/2017/01/27/what-is-tor-andwhy-do-people-use-it/#1d2614b7d752............17

Life Without Parole: America's New

Death Penalty? edited by

Charles J. Ogletree, Jr.,

Austin Sarat (2012) ..........................................8

Levi Pulkkinen,

Bellevue programmer gave up

$180k salary to deal drugs on

Silk Road, SeattlePI.com

(March 19, 2015, 12:38PM),

http://www.seattlepi.com/seattlenews/

article/Bellevue-programmer-gave-up180k-salary-to-deal-6144142.php) ...................8

Marvin E. Frankel,

Criminal Sentences: Law Without Order

New York: Hill and Wang, 1972 ....................13

Nate Raymond,

An alleged staff member of Silk Road 2.0

was sentenced to 8 years in prison,

BusinessInsider.com (Jun. 4, 2016,

4:42AM), http://www.businessinsider.com/

r-key-player-in-silk-road-successor-site-getseight-years-in-us-prison-2016-6)......................9

ix

Other Authorities Continued

Nate Raymond,

Silk Road member Peter Nash avoids

further US prison time,

The Sydney Morning Herald,

May 27, 2015 ....................................................8

Nicola Gennaioli and Andrei Shleifer,

Judicial Fact Discretion,

37 J. Legal Stud. 1 (2008) ..............................10

Nila Bala,

Judicial Fact-Finding in the

Wake of Alleyne, 39 N.Y.U. Rev. L.

& Soc. Change 1 (2015) ..................................11

Oral Argument,

U.S. v. Ulbricht, 858 F.3d 71

(2d Cir. 2016), available at

http://www.ca2.uscourts.gov/

decisions/isysquery/7fc49c36-9780-412b9fa0-2310e6e29d90/181-190/list/ ...................19

Paul F. Kirgis,

Sentencing Facts After Booker,

39 Ga. L. Rev. 895 (2005) .........................10, 12

Paul F. Kirgis,

The Right to a Jury Decision on

Sentencing Facts after Booker:

What the Seventh Amendment

Can Teach the Sixth,

39 Ga. L. Rev.897 (2005)

available at http://scholarship.law.

umt.edu/faculty_lawreviews/131 ...................15

x

Other Authorities Continued

Phillip Rogaway,

The Moral Character of Cryptographic

Work (Dec. 2015) Department of

Computer Science, University of California,

Davis, (2015 IACR Distinguished

Lecture), http://web.cs.ucdavis.edu/

~rogaway/papers/moral-fn.pdf .......................17

Press Release, U.S. Attorney's Office

Southern District of New York,

Operator of Silk Road 2.0 Website

Charged in Manhattan Federal

Court, Nov. 6, 2014

(available at https://www.fbi.gov/

contact-us/field-offices/newyork/news/pressreleases/operator-of-silk-road-2.0-websitecharged-in-manhattan-federal-court) ..............9

Reginald Rose,

Twelve Angry Men, Act III, 44-45 (1955) ......24

Robin Steinberg,

Heeding Gideon's Call in

the Twenty-First Century:

Holistic Defense and the

New Public Defense Paradigm,

70 Wash. & Lee L. Rev. 961 (2013) ................13

Roger Roots,

The Rise and Fall of the American Jury,

8 Seton Hall Cir. Rev. 1 (2011) ......................11

Stephanos Bibas,

Judicial Fact-Finding at Sentencing,

Faculty Scholarship,

U. Penn. Law School, 2008 ............................14

xi

Other Authorities Continued

Valerie P. Hans,

Deliberation and Dissent:

12 Angry Men Versus the Empirical

Reality of Juries, (2007),

Cornell Law Faculty Publications,

Paper 307 ........................................................23

1

STATEMENT OF INTEREST 1

Amici are organizations and a former judge committed to defending the constitutional protections afforded by both the Fourth and Sixth Amendments and

include the National Lawyers Guild, American Conservative Union Foundation Center for Criminal Justice Reform, Freedom Project, Judge Nancy Gertner

(Ret.), the Human Rights Defense Center, National

Coalition to Protect Civil Freedoms, the Partnership

for Civil Justice Fund, People’s Law Office. Many of

these organizations have appeared previously as amicus curiae before this Court. Their individual organizational statements are contained in the Appendix

following this brief.

SUMMARY OF ARGUMENT

This Court should accept certiorari because of the important concerns related to privacy and judicial factfinding in a context that suggests bias and hostility to

constitutionally protected viewpoints.

First, this case squarely presents the question of privacy interests in Internet browsing history. Whether

or not the government may obtain this information

without a showing of probable cause is a question of

tremendous importance for individual freedom and

political activity.

1 Rule 37 Statement: All parties received timely notice of amici’s

intent to file this brief and consented to its filing. No counsel for

any party authored any portion of this brief, and amici alone

funded its preparation and submission.

2

Second, this case raises important questions of what

factors may be legitimately considered by judges at

the sentencing phase. Petitioner’s sentence was based

on judicial fact-finding that the defendant commissioned murders, even though he was never charged

with any form of homicide or planning homicide and

there were no relevant jury findings. The judge also

expressed hostility to Petitioner’s philosophy and political views. This Court should not permit punishment based on lower burdens of proof for any crime,

much less one as serious as murder-for-hire, and

should clarify that punishments may not be enhanced

because of ideology.

ARGUMENT

I. THIS COURT SHOULD RESOLVE THE

QUESTION OF THE PRIVACY INTEREST IN

ONLINE ACTIVITY

This society is grappling with the question of what

privacy protections should attend modern communications in a free society. “[B]oth empirical research

and public opinion polls suggest that the public has

higher expectations of privacy than those recognized

by the courts in most Fourth Amendment jurisprudence.” Christine Scott-Hayward et al., Does Privacy

Require Secrecy? Societal Expectations of Privacy in

the Digital Age, 43 Am. J. Crim. L. 19, 49 (2015).

This Court has taken notice, providing important

guidance by revising decades-old principles in light of

new technology, Riley v. California, 134 S. Ct. 2473

(2014) (warrantless search incident to arrest may not

include search of digital information on the arrested

person’s cell phone), and confronting further

3

questions of when modern technology fundamentally

changes the nature of an intrusion into one that is unreasonable, Carpenter v. United States, 137 S. Ct.

2211 (2017) (granting cert. to resolve whether the

warrantless seizure and search of historical cell

phone records revealing the location and movements

of a cell phone user over the course of 127 days is permitted by the Fourth Amendment).

In working through these questions, this Court would

benefit from considering a fuller array of the types of

intrusions made possible when the third-party doctrine, as developed in Smith v. Maryland, 442 U.S.

735 (1979), is applied to types of activity that could

not have been envisioned by courts in decades past.

The court below held that government collection of information regarding the specific IP addresses that a

person visits is “precisely analogous to the capture of

telephone numbers at issue in Smith.” United States

v. Ulbricht, 858 F.3d 71, 97 (2d Cir. 2017) (citing

Smith v. Maryland, 442 U.S. 735 (1979)). But this is

far from self-evident and has been a subject of debate

and concern at this Court, in lower courts, and among

the general public.

In this Court, Riley, 134 S. Ct. at 2490, specified that

one reason a warrant was required for searches of mobile telephones, even in a search incident to arrest,

was because “[a]n Internet search and browsing history, for example, can be found on an Internet-enabled phone and could reveal an individual’s private

interests or concerns.” This echoes prior concerns and

still-open questions about the extent of legal protection for Internet activity that, to many, appears

4

extremely private. See, e.g., United States v. Jones,

565 U.S. 400, 417-18 (2012) (Sotomayor, J., concurring) (reasoning that simple application of the thirdparty doctrine “is ill suited to the digital age, in which

people reveal a great deal of information about themselves to third parties” such as “the URLs that they

visit” and observing that “I for one doubt that people

would accept without complaint the warrantless disclosure to the government of a list of every Web site

they had visited in the last week, or month, or year”).

The Eleventh Circuit’s concern and internal disagreement in United States v. Davis, 785 F.3d 498 (11th

Cir. 2015), regarding the applicability of Smith to web

browsing history is instructive. In dissent, Chief

Judge Martin was concerned that “blunt application

of the third-party doctrine threatens to allow the government access to a staggering amount of information

that surely must be protected under the Fourth

Amendment” including, specifically, “what websites

you access.” Id. at 535-36 (Martin, C.J., dissenting).

The majority acknowledged these concerns, but held

that it could not respond to them absent instruction

from this Court. Id. at 521 (“[a]s judges of an inferior

court, we have no business in anticipating future decisions of the Supreme Court. If the third-party doctrine results in an unacceptable ‘slippery slope,’ the

Supreme Court can tell us as much”).

Notably, studies reveal that actual expectations of

privacy in Internet histories are quite high. ScottHayward, supra at 54 (public opinion studies revealed

that “the expectation of privacy for Internet information was very high. Approximately 85% of respondents felt that law enforcement should never have

5

access or at least require a level commensurate with

probable cause to obtain information about online

search, purchase, website visitation histories”).

Accordingly, this case presents an opportunity for the

Court to address a type of modern activity—web

browsing—that has weighed heavily in recent thinking about privacy concerns but has not been resolved.

Moreover, as discussed below, the ability to access the

Internet without being monitored by the government,

absent probable cause, is essential to a modern free

society.

A. Online activity has extraordinary social

importance and requires constitutional

protection.

In addition to Fourth Amendment concerns, a free

and open Internet is essential to the marketplace of

ideas, Abrams v. United States, 250 U.S. 616, 630

(1919) (Holmes, J., dissenting), and the government’s

and lower court’s notion that there are no privacy interests to be protected in web browsing history has

alarming First Amendment implications. Although

the right to receive information is typically discussed

in the context of censorship, see, e.g., Stanley v. Georgia, 394 U.S. 557, 564 (1969) (“right to receive information and ideas”); Editorial, The Right to Receive

Ideas, Wash. Post, Apr. 12, 1969; Board of Education

v. Pico, 457 U.S. 853 (1982); ACLU v. Reno, 521 U.S.

844, 874 (1997) (holding that the Communications

Decency Act “effectively suppresses a large amount of

speech that adults have a constitutional right to receive”), it is a principle of which this Court should be

mindful when evaluating the importance of privacy

6

rights in Internet histories. “We are all familiar with

the thought that democracy requires a flourishing

‘public life.’ Less familiar, but equally essential, is the

idea that a self-governing people requires a flourishing personal life.” Jed Rubenfeld, The End of Privacy,

61 Stan. L. Rev. 101, 128 (2008); see also Human

Rights Watch, With Liberty to Monitor All: How

Large-Scale US Surveillance is Harming Journalism,

Law, and American Democracy, July 28, 2014.

It will be self-evident to many that what can be determined from examining only Internet histories is profoundly “private” information. As discussed above, examinations of online activity have been highlighted as

the type of intrusion into private matters that is of

concern when other types of government searches are

being considered by this and lower courts. Amici believe that the Court will find that the same interests

implicated in searches of a mobile phone also require

a warrant based on probable cause before the government may monitor an individual’s web history. Riley,

134 S. Ct. at 2493 (reflexively relying on “pre-digital

analogue[s]” risks “a significant diminution of privacy”).

However, the court below mechanically applied

nearly forty-year-old precedent, believing that cases

considering pen traps of the telephone number dialed

was akin to government knowledge of what websites

a person visits. Ulbricht, 858 F.3d at 97. Something

as socially, politically, and personally important as

website browsing history requires updated consideration of privacy rights by this Court before the government is given license to search it without probable

cause.

7

By granting cert. in this case, the Court would benefit

from full and precise briefing on this specific issue and

could clarify important rights for the public as well as

provide much-needed guidance for the lower courts.

See Davis, 785 F.3d at 521, 537.

II. TO ENSURE THAT JUDGES DO NOT UNFAIRLY PUNISH A DEFENDANT IN VIOLATION OF THE SIXTH AMENDMENT TO THE

U.S. CONSTITUTION, SENTENCES MUST

BE BASED ON FACTS PROVEN AT TRIAL

Judges, when poised to render sentencing, should not

engage in fact-finding. This Court held in Apprendi v.

New Jersey that the Sixth Amendment right to a jury

trial—a “constitutional protection[] of surpassing importance”— prohibits judges from enhancing criminal

sentences beyond statutory maximums based on facts

other than those decided by the jury beyond a reasonable doubt or fact of prior conviction. Apprendi v. New

Jersey, 530 U.S. 466, 476 (2000). Antipathy to entrusting the government with sentencing has existed

since the nation’s founding, preferring the “unanimous vote of 12 of [their] fellow citizens.” Id. at 498

(Scalia, J., concurring).

The extraordinary harshness of the sentence in this

case, based on especially problematic judicial factfinding, calls for careful scrutiny. Thirty-one-yearold Ross William Ulbricht, a first-time offender, received a much harsher sentence than prosecutors

sought based not on charges presented to the jury, but

rather on judicially-found “facts”—namely that he ordered several murders-for-hire. C.A. App. 1464-1466.

Although Mr. Ulbricht’s case was not death-penalty

8

eligible, his sanction of life without possibility of parole, also referred to as “death-in-prison,” is close on

the punishment spectrum, and is “severe and degrading, arbitrarily imposed, and ha[s] been condemned

by members of the international community.” Life

Without Parole: America's New Death Penalty? edited by Charles J. Ogletree, Jr., Austin Sarat at 66-67

(2012). 2

It is worth noting that other Silk Road-related defendants received significantly lighter sentences, ranging

from ten years to 16 days, in disregard of the sentencing consideration to avoid unwarranted sentencing

disparities among defendants with similar records

who have been found guilty of similar conduct. 3 18

U.S. Code Sec. 3553.

2 It is likely that this nation’s framers could not have antici-

pated the vast expansion of a life-sentenced prison population. More than 200,000 persons—one out of every seven individuals incarcerated in the United States—are serving life

or “virtual life” sentences (named for the proposition that

they will realistically never be released), Ashley Nellis, Still

Life America’s Increasing Use of Life and Long Term Sentences, The Sentencing Project, May 3, 2017, available at

https://www.sentencingproject.org/publications/still-lifeamericas-increasing-use-life-long-term-sentences/.

3 Peter Nash, Silk Road moderator, received a sentence of 17

months. See Nate Raymond, Silk Road member Peter Nash

avoids further US prison time, The Sydney Morning Herald, May

27, 2015. Jan Slomp, “biggest” Silk Road drug dealer, received

a sentence of 10 years. See Jason Meisner, Biggest dealer on underground Silk Road given 10 years in prison, Chicago Tribune,

May 29, 2015. Steven Sadler, “top” Silk Road drug dealer, received a sentence of 5 years. See Levi Pulkkinen, Bellevue programmer gave up $180k salary to deal drugs on Silk Road,

9

The case of Blake Benthall, alleged owner and operator of Silk Road 2.0—one of many dark net markets

that proliferated after Ulbricht’s sentencing 4—illustrates the gross disparity. In its press release after

Benthall’s arrest on November 5, 2014, the FBI noted:

Silk Road 2.0 was virtually identical to the

original Silk Road website in the way it appeared and functioned. In particular, like

its predecessor, Silk Road 2.0 operated exclusively on the “Tor” network and required

all transactions to be paid for in Bitcoins in

order to preserve its users’ anonymity and

evade detection by law enforcement.

Press Release, U.S. Attorney's Office Southern District of New York, Operator of Silk Road 2.0 Website

Charged in Manhattan Federal Court, Nov. 6, 2014

SeattlePI.com (March 19, 2015, 12:38PM), http://www.seattlepi.com/seattlenews/article/Bellevue-programmer-gave-up180k-salary-to-deal-6144142.php). Jason Hagen, Silk Road

“global meth dealer,” received a sentence of 3 years. See Bryan

Denson, Global meth dealer from Vancouver gets lighter sentence

because of U.S. agents' 'Silk Road' corruption, The Oregonian/OregonLive (Nov. 5, 2015, 3:15PM), http://www.oregonlive.com/pacific-northwest-news/index.ssf/2015/11/global_silk_road_meth_dealer_f.html).

Brian

Farrell, “key assistant” to Silk Road 2.0’s owner/operator Blake

Benthall, received a sentence of 8 years. See Nate Raymond, An

alleged staff member of Silk Road 2.0 was sentenced to 8 years in

prison, BusinessInsider.com (Jun. 4, 2016, 4:42AM),

http://www.businessinsider.com/r-key-player-in-silk-road-successor-site-gets-eight-years-in-us-prison-2016-6).

4Andy Greenberg, The Silk Road Creator’s Life Sentence Actually Boosted Dark Web Drug Sales, (May 23, 2017, 10:00AM),

https://www.wired.com/2017/05/silk-road-creators-life-sentenceactually-boosted-dark-web-drug-sales/.

10

(available at https://www.fbi.gov/contact-us/field-offices/newyork/news/press-releases/operator-of-silkroad-2.0-website-charged-in-manhattan-federalcourt).

U.S. Attorney Preet Bharara also acknowledged Benthall was running “a nearly identical criminal enterprise” to Silk Road. Id. Yet, Benthall spent a mere 16

days in prison while Petitioner is serving a life sentence. Federal Bureau of Prisons, Find An Inmate

[Blake Benthall, Register No. 20045-111, released

Nov. 21, 2014], https://www.bop.gov/inmateloc/, (last

visited Jan. 27, 2018).

While judicial fact-finding was historically initiated

to afford judges a vehicle for lowering sentences, it

has evolved to do the opposite. Paul F. Kirgis, Sentencing Facts After Booker, 39 Ga. L. Rev. 895 (2005).

It also taints the criminal justice process as a whole

in that “fact discretion not only creates leeway for the

expression of judicial biases, it also undermines the

appeals process and adversarial litigation. Although

these mechanisms are sometimes believed to put a

beneficial check on trial courts, under fact discretion

they lose their effectiveness.” Nicola Gennaioli and

Andrei Shleifer, Judicial Fact Discretion, 37 J. Legal

Stud. 1, 4 (2008).

It is not problematic that the judge considered background information beyond the conviction, but it is of

concern that new, uncharged offenses were brought

up at sentencing and informed the ultimate sentence,

in violation of the Sixth Amendment. “The challenge

arises in line-drawing to permit suitable judicial discretion while cabining the ability of judges to punish

11

uncharged and acquitted conduct.” Nila Bala, Judicial Fact-Finding in the Wake of Alleyne, 39 N.Y.U.

Rev. L. & Soc. Change 1 (2015). The Sixth Amendment jury right provides that an individual should not

be punished for an uncharged offense because that

person has been convicted of another crime. United

States v. Booker interprets the Sixth Amendment as

requiring that any fact used to impose a sentence

longer than the longest sentence be supported by the

jury finding or guilty plea must be proved to a jury or

admitted by the defendant. 543 U.S. 220, 133 (2005).

A. Jurors’ historic role as a check against

unbridled judicial power has diminished,

to the detriment of the rule of law.

This case makes evident how the American jury’s

role—as “populist protector” and a check against tyranny—has become but a "shadow of its former self,"

with sentencing practices vesting increasing power in

judges despite the constitutional mandate that the

jury be central to reaching a judgment. Akhil R.

Amar, The Bill of Rights: Creation & Reconstruction

83 (1998).

This nation’s Framers and Founders feared the vagaries of judicial discretion. Roger Roots, The Rise

and Fall of the American Jury, 8 Seton Hall Cir. Rev.

1, 3 (2011). They were explicit that trial by jury was

necessary to thwart and obstruct judges, not merely

prosecutors with weak cases. Elbridge Gerry insisted

that jury trials were necessary to guard against corrupt judges. Id. Alexander Hamilton echoed this concern when he wrote, “The strongest argument in [trial

by jury's] favour is, that it is a security against

12

corruption.” Id. John Adams said that it was a juror's

duty to “find the verdict according to his own best understanding, judgment and conscience, though in direct opposition to the direction of the court.” 2 John

Adams's Works, 254, 255 (1771).

This Court has long reaffirmed the Founders’ contention that juries’ role is paramount to the execution of

justice: "The jury system postulates a conscious duty

of participation in the machinery of justice.... One of

its greatest benefits is in the security it gives the people that they, as jurors actual or possible, being part

of the judicial system of the country can prevent its

arbitrary use or abuse." Balzac v. Porto Rico, 258 U.S.

298, 310 (1922).

In the late 20th century, criminal sentencing changed

in two significant ways that diminished juries’ power:

(1) New statutory schemes provided for different penalties for a single crime depending on the existence of

aggravating circumstances, and (2) judges were afforded discretion to set sentences within board penalty ranges (indeterminate sentencing). Paul F. Kirgis, Sentencing Facts After Booker, 39 Ga. L. Rev. 895

(2005).

“With respect to the second type of innovation, courts

and commentators seem to have failed to recognize

the potential for incursion into the jury’s traditional

bailiwick.” That can be attributed to the fact that

these reforms were designed to reduce, not increase,

sentences, making them flexible so that offenders

could be released when rehabilitated. Id. at 909.

13

With the introduction of the Sentencing Guidelines in

1986, and statutory sentencing schemes in many

states, the issue that had until then been latent—judicial fact-finding in sentencing—rose to the fore.

The guidelines were designed to minimize judicial discretion—thought to be too lenient—and amounted to

a retribution model replacing the former rehabilitation model of punishment. Judicial fact-finding no

longer worked in favor of the defendant. In early

cases, challenging judicial fact-finding under the

Guidelines and state counterparts, this Court did not

signal that it would find any constitutional problems

with the new sentencing framework.

While there have been efforts to reform sentencing

practices over the past four decades, this Court should

consider the instant case in light of the values informing this nation’s founding. Judge Marvin Frankel persuasively explicated modern considerations that augment reasons the founders might have been concerned with judicial fact-finding: factors such as class,

education, and race influence judges. He wrote: “The

almost wholly unchecked and sweeping powers we

give to judges in the fashioning of sentences are terrifying and intolerable for a society that professes devotion to the rule of law.” Marvin E. Frankel, Criminal

Sentences: Law Without Order. New York: Hill and

Wang, 1972.

The right to have a sentence based on proven facts remains a central concern today, and this case presents

an opportunity for the Court to clarify the limits of

judicial fact-finding at sentencing. See gen’ly, Robin

Steinberg, Heeding Gideon's Call in the Twenty-First

14

Century: Holistic Defense and the New Public Defense

Paradigm, 70 Wash. & Lee L. Rev. 961, 963 (2013).

B. Sentencing must be limited to facts admitted by the defendant or supported by jury

findings.

Significantly for the instant case, this Court precluded judges from enhancing criminal sentences

based on facts other than those decided by the jury or

admitted by the defendant in part out of a concern

that “[w]hen a judge inflicts punishment that the

jury’s verdict alone does not allow, the jury has not

found all the facts ‘which the law makes essential to

the punishment,’ and the judge exceeds his proper authority.” Blakely v. Washington, 542 U.S. 296, 303

(2004), quoting 1 J. Bishop, Criminal Procedure § 87,

p 55 (2d ed. 1872); see also Stephanos Bibas, Judicial

Fact-Finding at Sentencing, Faculty Scholarship, U.

Penn. Law School, 252, 2008).

It is instructive to recall Justice Scalia’s words regarding Mr. Blakely’s enhanced sentence and the

stakes involved:

The Framers would not have thought it too

much to demand that, before depriving a

man of three more years of his liberty, the

State should suffer the modest inconvenience of submitting its accusation to the

unanimous suffrage of twelve of his equals

and neighbours, rather than a lone employee of the State.

15

Blakely, slip op. at 313 (internal quotation marks and

citation omitted).

As our system has implicitly recognized for

centuries, juries are simply the best actors

to decide fact questions. Fact questions involved speculative judgments about unknown events. In order to allow the parties

and the legal system to put disputes behind

them, adjudication must result in final determinations about the matters contested

by the parties. Only the jury, with its veiled,

democratic decision-making structure, has

the societal imprimatur to render acceptable final decisions on matters that are inherently unknowable.

Paul F. Kirgis, The Right to a Jury Decision on Sentencing Facts after Booker: What the Seventh Amendment Can Teach the Sixth, 39 Ga. L. Rev.897, 905

(2005).

The district court judge in this case failed to set forth

a reasoned basis for considering several alleged drugrelated deaths as relevant facts to be considered in

determining Mr. Ulbricht’s sentence. See Rita v.

United States, 551 U.S. 338, 356 (2007). Judge Forrest

based her sentence on unestablished facts that Mr.

Ulbricht’s actions “somehow related to” alleged drug

overdose fatalities. C.A. App. 1472-1480. This was despite a report by Board-certified forensic pathologist

defense expert, Mark L. Taff, M.D., that found insufficient information to attribute any of the deaths to

drugs purchased from Silk Road vendors. C.A. App.

904. The government did not rebut Dr. Taff’s report,

16

and nothing in the jury verdict resolved this contested

fact.

C. Judicial fact-finding in this context is particularly troublesome and certiorari presents an appropriate vehicle to address

this issue.

1. Confusion and fear, related to misunderstood technology, and highly prejudicial

murders-for-hire and drug-related fatalities, impermissibly tainted sentencing

The sentence was based on judicial findings related to

allegations of serious crimes that not only were never

found by a jury but were not even among the charges

leveled at trial. During closing argument, the U.S. attorney explicitly advised the jury: “[T]o be clear, the

defendant has not been charged for these attempted

murders here. You’re not required to make any findings about them. And the government does not contend that those murders actually occurred.” Trial Tr.

2159:25-2160:3, Feb. 3, 2015.

Thus, these “found” murders-for-hire and other

harms are best understood as anxious imaginings of

the darker intentions that “must” lurk behind the

commonly misunderstood Silk Road technologies,

namely anonymizing software, crypto-currency, and

the so-called Dark Web. Despite widespread and

growing use of Tor and Bitcoin, United States law enforcement’s framing of surveillance and cryptography

shapes how the mainstream sees it. Privacy and national security are depicted as being in conflict, with

emerging communications technology an asset to

17

privacy and a setback to security. Encryption is portrayed as especially threatening because law enforcement techniques have not kept apace. “It is a brilliant

discourse of fear: fear of crime; fear of losing our parents' protection; even fear of the dark.” Phillip

Rogaway, The Moral Character of Cryptographic

Work (Dec. 2015) Department of Computer Science,

University of California, Davis, essay written to accompany an invited talk (the 2015 IACR Distinguished Lecture) given at Asiacrypt 2015 on December 2, 2015, in Auckland, New Zealand,

http://web.cs.ucdavis.edu/~rogaway/papers/moralfn.pdf (last visited Jan. 25, 2018).

It is tempting to believe the sweeping generalizations

that the Dark Web is solely a terrain of lawlessness,

with Bitcoin and Tor serving as criminals’ saddle and

spurs. Law Enforcement Struggles to Police “Dark

Web,” IACPCybercenter.com, http://www.iacpcybercenter.org/news/law-enforcement-struggles-policedark-web/ (last visited Jan. 27, 2018). Two years after

the trial, these three areas remain widely misunderstood, and shrouded in mystery and sensationalism,

despite the fact that many legitimate users abound:

journalists, dissidents, and the military. Lee Matthews, What Is Tor, And Why You Should Use It To

Protect Your Privacy, Forbes.com (Jan. 27, 2017,

2:30PM),

https://www.forbes.com/sites-/leemathews/2017/01/27/what-is-tor-and-why-do-peopleuse-it/#1d2614b7d752.

18

2. Constitutionally irrelevant victim impact

statements factored into sentencing bias

Such misunderstandings or confusion about technology were augmented by impact witness statements at

sentencing by parents of alleged Silk Road consumers

who suffered fatalities. C.A. App. 1472-1496. Victim

impact testimony may be prejudicial in that it diverts

attention away from the facts that must be scrutinized, such as the circumstances surrounding the

crime and the defendant’s background and character.

Bryan Myers and Edith Greene, The Prejudicial Nature of Victim Impact Statements: Implications for

Capital Sentencing Policy, 10 Psych. Pub. Pol. & L.

492 (2004).

Victim impact testimony creates “the risk that

a…sentence will be based on considerations that are

‘constitutionally impermissible or totally irrelevant to

the sentencing process” by focusing on the character

of the victim and his or her experience, rather than

that of the offender. Booth v. Maryland, 482 U.S. 496,

502 (1987) (citing Zant v. Stephens, 462 U.S. 862, 885

(1983)).

This Court has noted that it would be difficult—if not

impossible—to provide a fair opportunity to rebut

such evidence without shifting the focus of the sentencing hearing away from the defendant.” Id. at 506.

The information may be so emotion-laden that jurors

and judges become more persuaded by how they feel

about the testimony than by the relevant case facts.

There are few more emotionally-charged and compelling witnesses than grieving parents. And no testimony is more prejudicial and irrelevant. Moreover,

19

the testimony in this instance concerns events for

which Mr. Ulbricht was not found criminally culpable.

Even the appellate court panel found certain testimony related to uncharged crimes inappropriate,

with Judge Gerald Lynch concerned that testimony

from parents of alleged Silk Road customers who died

“put an extraordinary thumb on the scale that shouldn't be there…. Does this [testimony] create an enormous emotional overload for something that's effectively present in every heroin case?” Lynch asked.

“Why does this guy get a life sentence?” He went on to

call the sentence “quite a leap.” Oral Argument at

27:00-29:18, U.S. v. Ulbricht, 858 F.3d 71 (2d Cir.

2016), available at http://www.ca2.uscourts.gov/decisions/isysquery/7fc49c36-9780-412b-9fa02310e6e29d90/181-190/list/.

Judge Forrest also pointed to evidence not charged at

trial that “Dread Pirate Roberts,” or “DPR,” paid to

have several persons murdered. Not one murder was

carried out, nor was Ulbricht charged in connection

with the alleged plots. Yet at the sentencing hearing

the trial judge asserted, “I find there is ample and unambiguous evidence that [Ulbricht] commissioned...murders to protect his commercial enterprise." C.A. App. 1464-1465.

In sum, a lack of understanding of the technology-related issues, coupled with uncharged crimes of murder-for-hire and emotion-laden witness impact testimony from grieving family members, were used at

sentencing to turn Petitioner into a composite of everything we have to fear about the Dark Web. Failure

to allow explanations of cryptocurrency, the Dark

20

Web, and Tor virtually ensured that the judge’s own

biases would go unchecked.

D. Judicial Expressions Of Hostility To Petitioner’s Ideology Undermines First

Amendment Values And Public Perception Of Fairness.

The fact that Mr. Ulbricht at one time opposed United

States drug laws is not relevant to his sentence, although it appeared to weigh heavily in the judge’s

thinking during sentencing. The Court should accept

cert. in this case to clarify that sentences based on judicial dislike of ideology cannot be tolerated.

The defendant’s ideological speech was related to a

five-decades-old government “war on drugs in the

United States [that] has been a failure that has ruined lives, filled prisons and cost a fortune.” George P.

Shultz and Pedro Aspedec, The Failed War on Drugs,

New York Times, Op Ed, Dec. 31, 2017.

When discussing Mr. Ulbricht’s character, the trial

court voiced disapproval of his political and philosophical views. Alluding to anonymous comments on

the Silk Road site, the judge said, “[T]here are posts

that discuss the laws as the oppressor and that each

transaction is a victory over the oppressor. This is

deeply troubling and terribly misguided and also very

dangerous.” A 1516. Before pronouncing Mr. Ulbricht’s sentence, the district court also expressed

concern that “the reasons that you started Silk Road

were philosophical and I don't know that it is a philosophy left behind.” A 1534.

21

The First Amendment guarantees expression of opinions on matters of public concern free from the fear of

legal punishment based on the viewpoint expressed.

The First Amendment reflects our “profound national

commitment to the principle that debate on public issues should be uninhibited, robust, and wide-open.”

New York Times Co. v. Sullivan, 376 U.S. 254, 270

(1964). “If there is a bedrock principle underlying the

First Amendment, it is that the government may not

prohibit the expression of an idea simply because society finds the idea itself offensive or disagreeable.”

Texas v. Johnson, 491 U.S. 397, 414 (1989).

Thus, adding to the concerns discussed in the preceding section that Mr. Ulbricht was sentenced for acts

that a jury did not find him responsible for, there is

strong reason for concern that he was punished for

the political views he held. All this, moreover, flows

from intrusion into his private web browsing history

without a prior showing of probable cause, as discussed in part I. Each of these concerns, and certainly

cumulatively, warrant attention from this Court.

E. Fact-Finding Should Be Entrusted To Juries, Not Judges.

In Duncan v. Louisiana, 391 U.S. 145, 156 (1968), this

Court unequivocally affirmed the crucial right to factfinding by jury:

Those who wrote our constitutions knew

from history and experience that it was necessary to protect against unfounded criminal charges brought to eliminate enemies

and against judges too responsive to the

22

voice of higher authority.… Providing an accused with the right to be tried by a jury of

his peers gave him an inestimable safeguard against the corrupt or overzealous

prosecutor and against the compliant, biased, or eccentric judge.

In his time-honored work, Democracy in America,

Alexis De Tocqueville exalts the jury system as one of

the most critical political institutions for democratic

self-government. Jury service not only educates citizens about the legal system, it also inculcates a sense

of their duties as citizens and, optimally, improves

their deliberations as citizens. Thus, juries have an

important structural and historical role. Jury participation in the criminal justice process is, in itself, an

important civic institution. De Tocqueville said that

the jury

places the real direction of society in the

hands of the governed…and not the government…. He who punishes the criminal is

therefore the real master of society.... All

the sovereigns who have chosen to govern

by their own authority, and to direct society,

instead of obeying its direction, have destroyed or enfeebled the institution of the

jury.

Alexis De Tocqueville, Democracy in America, 361,

362 (The Century Co. 1898, 1st ed.).

Further, in The American Jury—a seminal book in

the study of juries’ influence in helping the public understand and appreciate the jury as an institution—

23

the authors’ overall observation was that “[w]hether

or not one comes to admire the jury system as much

as we have, it must rank as a daring effort in human

arrangement to work out a solution to the tensions

between law and equity and anarchy.” Harry Kalven,

Jr. and Hans Zeisel, The American Jury, 499 (1966).

When civics was taught in American schools, teachers

frequently screened the classic play and film 12 Angry

Men (Orion-Nova 1957) to illustrate the criminal justice system. The characters, identified by their juror

numbers, are often described as archetypes of human

qualities working together in search of truth and justice. The process of collective deliberation and voting

tempers individual bias. “[T]he wisdom and insights

of 12 Angry Men find support in empirical studies of

the contemporary jury. The value of diversity in promoting vigorous and fruitful discussion and the power

of jury deliberation in forcing deeper thinking are

both reinforced by social science studies of decision

making.” Valerie P. Hans, Deliberation and Dissent:

12 Angry Men Versus the Empirical Reality of Juries,

(2007), Cornell Law Faculty Publications, Paper 307

at 589.

In the play, jurors number Eleven and Nine have a

brief exchange on their collective and personal responsibility:

ELEVEN: …. We have a responsibility. This

is a remarkable thing about democracy.

That we are—what is the word?—ah, notified! That we are notified by mail to come

down to this place—and decide on the guilt

or innocence of a man; of a man we have not

24

known before. We have nothing to gain or

lose by our verdict. This is one of the reasons

why we are strong. We should not make it a

personal thing….

NINE: [slowly] Thank you very much.

ELEVEN: [slight surprise] Why do you

thank me?

NINE: We forget. It’s good to be reminded.

Reginald Rose, Twelve Angry Men, Act III, 44-45

(1955).

CONCLUSION

For the foregoing reasons, amici curiae respectfully

urge this Honorable Court to grant certiorari in this

matter and reverse the decision below.

25

Respectfully submitted,

Heidi Boghosian

Counsel of Record for Amici

A.J. MUSTE MEMORIAL

INSTITUTE, INC.

168 Canal Street, 6th Fl

New York, NY 10013

(917) 239-4999

Prof. Zachary Wolfe

The George Washington

University

2100 Foxhall Rd, NW

Ames Hall 218

Washington, DC 20007

zwolfe@gwu.edu

(202) 242-5130

February 5, 2018

This is a copy of a public record, reproduced as it was published. It is not legal advice, and it may not be the version a court would rely on. Check the official source before you cite it.

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